Water → HCID 10426318, compound

HRID 1440353Notes

Reaction equation

HRID 1440353 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[NH:13][C:14](=[O:16])[CH3:15].F[B-](F)(F)F.[O:22]=[N+:23]=[O:24].O>C(#N)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4]([N+:23]([O-:24])=[O:22])=[CH:5][CH:6]=[C:7]2[NH:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 10084913HCID 10084913, compoundHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 10426318HCID 10426318, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a cold (-5° C.) suspension of 4.45 g (16.00 mmol) of compound (19) in 25 ml acetonitrile was added dropwise a suspension of 2.60 g (16.64 mmol) of nitronium tetrafluoroborate in 5 ml of acetonitrile. After ten minutes, the homogenous, light-yellow reaction mixture was poured into water and extracted twice with ethyl acetate. The combined organic layers were washed with saturated NaCl solution and then dried over anhydrous MgSO4. The solvent was then removed under reduced pressure, and the crude residue was recrystallized from methanol to give N-(5-bromo-8-methyl-4-nitro-naphthalen-1-yl)-acetamide (20) as a light-yellow solid, m.p. 216°-217° C. Another 0.80 g of compound (20) was obtained from the concentrated mother liquors after flash chromatography on silica, eluting hexanes:ethyl acetate (1:1). The overall yield was 2.00 g (39%).

Workup

  1. additionwas added dropwise
  2. waitAfter ten minutes
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed with saturated NaCl solution
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was then removed under reduced pressure
  7. customthe crude residue was recrystallized from methanol

Sources & evidence

ORD record
ord-0142eb8892114e178d07601086255acc
Source dataset
uspto-grants-1996_03
Patent number
US05498727

Reaction notes

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